4. The word 'umpolung' is literally German for 'polarity reversal'. It is a concept in organic chemistry in which a polar covalent bond can be 'reversed'. A great example of this is the reaction between an aldehyde and 1,3-propanedithiol to yield a dithiane. The aldehyde proton is nonacidic whatsoever. But the very same proton, once converted into the dithiane, has a pKa ca. 30. So, it can be deprotonated. The resulting carbanion can be used as a nucleophile, as shown below. Provide mechanisms for the reactions below. umpolung chemistry H. aldehyde ketone HS SH 1, Buli S. H,O H,SO, (cat) 2. bromobutane Ph Ph
4. The word 'umpolung' is literally German for 'polarity reversal'. It is a concept in organic chemistry in which a polar covalent bond can be 'reversed'. A great example of this is the reaction between an aldehyde and 1,3-propanedithiol to yield a dithiane. The aldehyde proton is nonacidic whatsoever. But the very same proton, once converted into the dithiane, has a pKa ca. 30. So, it can be deprotonated. The resulting carbanion can be used as a nucleophile, as shown below. Provide mechanisms for the reactions below. umpolung chemistry H. aldehyde ketone HS SH 1, Buli S. H,O H,SO, (cat) 2. bromobutane Ph Ph
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
Related questions
Question
Explain the mechanisms
Transcribed Image Text:2 CH;LI
?
3. HO*
EIO-
EtO
(17-methyltestosterone
(an anabolic steroid))
4. The word 'umpolung' is literally German for 'polarity reversal'. It is a concept in
organic chemistry in which a polar covalent bond can be 'reversed'. A great
example of this is the reaction between an aldehyde and 1,3-propanedithiol to yield
a dithiane. The aldehyde proton is nonacidic whatsoever. But the very same
proton, once converted into the dithiane, has a pKa ca. 30. So, it can be
deprotonated. The resulting carbanion can be used as a nucleophile, as shown
below. Provide mechanisms for the reactions below.
H umpolung chemistry
aldehyde
ketone
1, Buli
s H,0
HSO, (cat)
2. bromobutane
Ph
PrtScn
Home
End
96
5n
6.
Expert Solution
Step 1
Step 1: ketone is protected using dithiane. Then dithiane proton is removed using BuLi resulted anion. anion attacks on butyl bromide results the product. Then dithiane is remove using acid gives the ketone.
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